The Good Life

Money Matches

Tiger taking on Phil with millions of dollars on the line was a new chapter in a long tradition of big-money games featuring golf’s biggest stars
| By Jeff Williams | From The Bond Legacy, July/August 2020
Money Matches
Photo/Christian Petersen via Getty Images
The final holes of “The Match,” pitting Tiger Woods against Phil Mickelson in 2018, were played in near darkness. The $9 million prize (in hundred-dollar bills) ultimately went to Mickelson.

When Tiger Woods and Phil Mickelson teed it up for 10 million bucks this past May, there was pride on the line for the old rivals, but not money. Woods, paired with Peyton Manning, and Mickelson, with partner Tom Brady, were playing for charity, and the millions at stake would go to pandemic relief efforts, not to them. Tiger and Manning won “The Match 2,” but not the oversized check.

But back in 2018, things were quite different, and the cash on the line was all for the victor. The original “Match” pitting Tiger versus Phil, one-on-one, had $9 million on the line and it was winner take all. That was real money, a pile of hundreds stacked on a table with a red cloth for all to see, and it all ended up in Phil’s pocket when he won on the fourth extra hole at Shadow Creek outside of Las Vegas, under the lights, no less. 

Phil and Tiger’s first high-profile money game harkened back to the grand days of exhibition golf on television beginning in the 1960s. “Shell’s Wonderful World of Golf” had two top players matched at iconic courses around the world; “Big Three Golf,” put together by IMG founder and superagent Mark McCormick, featured Arnold Palmer, Jack Nicklaus and Gary Player; and then came the outrageously successful Skins Game, which began in 1983 with the Mount Rushmore of players—Palmer, Nicklaus, Player and Tom Watson. The skins those stars played for were titanic payouts for the time, money that far eclipsed what they could make in a typical tournament. These were money games with deep impact.

Woods and Mickelson were the “Twin Peaks” of the game in 2018 when the big-money match was arranged for November 23, the day after Thanksgiving. The men were playing for an enormous sum of money, greater than the usual total purse for a standard PGA event. 

With the two competitors worth hundreds of millions each, some might dismiss the impact of the cash prize, but this was a payout for the record books. The victor at a major tournament typically walks home with about $2 million. This year, The Players Championship boosted its winner’s purse to $2.7 million, the richest prize for a single tournament in golf. (The event was canceled after the first round this year.) The FedEx Cup pays a cool $15 million, but that’s a reward for an entire season. Nine million dollars on the line for one day of play, winner take all? There was nothing like it before or since in the world of golf.

The match seesawed the whole way, with Mickelson 1-up playing the 17th hole. Woods’ tee shot on the par 3 flew into the back rough while Mickelson knocked it to 11 feet. Then Woods holed the chip and Mickelson missed his putt, sending the match all square to the 18th. Woods could have won with an eight-footer for birdie, but he missed. He then graciously conceded Mickelson’s four-footer for par, sending the match to extra holes. They played the 18th again, with a pair of birdies in the darkness that forced the game to move to a makeshift, lighted par 3 of 95 yards, hitting from the practice putting green back to the 18th green.

The second time they played it, Woods pitched long while Mickelson stuck it to six feet. Woods failed to make his chip and had a five-footer left. When Mickelson missed his shorty, he gave Woods the five-footer, uttering the most poignant words of the day: “I don’t want to win like this.”

Mickelson won it the third time they played the hole, doing so, as he would say: “The way I think we both wanted to win it, by making birdie.” For Mickelson, who spent the bulk of his career in Woods’ immense shadow, there was satisfaction as he admired the stacks of $100 bills at the awards ceremony. An undesignated portion of the $9 million went to his foundation and several charities, and plenty went to taxes, but the rest was all his. There’s no word how he spent the cash.

“I know, big picture, your career is the greatest of all time. I’ve seen you do things that are just remarkable,” said Mickelson. “But just know I will not ever let you live this one down. I will bring it up every time I see you… It’s not the Masters, it’s not the U.S. Open, I know, but it’s something. It’s just nice to have a little something on you.”

While there was a modicum of entertainment in “The Match,” the golf was hardly sterling and the expected trash talking between the two mic’d-up players never really materialized, quite unlike the second version held this year (see sidebar, page 80). But even that paled in comparison to the level of excitement that the original Skins Game brought to golf’s expanding television window in the early 1980s.

The Skins Game was held each weekend after Thanksgiving, nine holes a day. When it began, there was $360,000 on the line, a gigantic purse for its time. For the first one in 1983, Palmer’s birdie on the 12th won him $100,000, which was more than double the prize money he had ever received for winning a tournament. Gary Player won $150,000 for a birdie on the 17th. If you think Woods and Mickelson were eager to win $9 million in 2018, consider what $150,000 meant to Gary Player in 1983. 

His final major win was the 1978 Masters, and he won $45,000. Winning $150,000 in 1983 was enormous. He made birdie on the 17th hole to earn those skins, and on the 18th tee, the nine-time major winner was shaking. He “was hyperventilating so bad on the 18th tee that he could hardly take the club back,” said Skins Game founder Don Ohlmeyer. “He could not believe he’d won that much money.” 

But that’s not all that first Skins Game is remembered for.

After the round (this part was not televised), Watson accused Player of cheating on the 16th hole by removing a living leaf from behind his ball, according to the late, great New York Times columnist and golf nut Dave Anderson, who wrote about overhearing their conversation. ‘‘I’m accusing you, Gary…you can’t do that…I’m tired of this…I wasn’t watching you, but I saw it,’’ Anderson reported Watson saying. “I was within the rules,” Player said, according to Anderson. 

Watson did not comment to the media and no action was taken. And despite the contretemps, the broadcast was an enormous success. For its first 10 years of existence, the Skins Game boasted better ratings than the U.S. Open over that span. The Skins Game held in 1986 was the highest-rated televised golf tournament of the season, the year that Nicklaus famously won his sixth and final Masters.

As the Big Three dropped out of the competition, other superstars gladly stepped in and the prize money increased. In 1987, the ever-chatty Lee Trevino made an ace worth $175,000, part of a $310,000 payday. Trevino’s comment was uncharacteristically short and sweet: “It looked like a Rembrandt.”

Fred Couples, the King of Cool, won a record $4.4 million in 14 career appearances, making him the King of Skins. In 2001, Greg Norman won the entire $1 million pot, skunking Woods, Colin Montgomerie and Jesper Parnevik. In 2005, Fred Funk lost a gimmick wager to Annika Sörenstam when she outdrove him, requiring Funk to play out the hole wearing a pink skirt. He got over his embarrassment by collecting nearly $1 million in skins.

Despite his legendary career, Woods never did win a Skins Game in seven appearances. The closest he came was 2004 when he lost on the fourth extra hole of a playoff to Couples. In the 2002 Skins Game he flinched on a bunker shot when a spectator’s camera went off at the top of his backswing. Woods’ caddie at the time, Steve Williams, snatched it from the spectator and threw it into the pond next to the green.

The Skins Game eventually lost its popularity, along with its stars. The skyrocketing purses of the PGA Tour in the Tiger Era and the need for time off at the end of the season for the game’s big names produced low-profile fields at the end of the year. K.J. Choi won the final production in 2008. 

Now if only we could somehow rekindle the great exhibitions of the past where there was so much money on the line that players—even the greats—had sweaty palms, twitchy knees and balky backswings. Those would be the good ole days, again.


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